Darlene Lost The Bet

My wife of thirty plus years and I started playing some card games that led to more tantalizing games to a game of poker that has continued for years with some amazing stakes. Some years back it all started out tame enough but over the years our stakes have become real kinky. We both really love the excitement and this has added a new dimension to our lives that has us both loving each other more than ever.

Our stakes or bets started out with simple things such as massages and as time went on the bets began to escalate to truth or dare type bets. During these sensual games of poker the stakes were getting so serious that if we thought it was too much we began to renege on the bets and that took a lot of the fun out of the games.

We knew that the stakes would eventually get to areas of our own demons and that a deep discussion was needed. During our talks there were very nervous comments and the conversations at times felt more like a confession about fantasies we had, but in the end we both agreed that we were ok with the new no limit stakes, so it was decided that there could be no more refusals, no matter what was asked of the other party. We knew that we were in uncharted territory with our relationship and marriage and as they say in the gambling world "the price of poker just went up........" I knew from our talks that she was a lot more stable in our relationship and she also wanted to "experiment" a lot more than I think I did. I wasn't sure if I could handle this but I thought I would give it a try and see just how far I would let my desires overrule my fears and jealousy.

I didn't want to sound like one of those goofy guys and describes his wife as the vixen only dreamed of, but I have to tell you that my wife doesn't look a day over thirty five and is the desire of all of my coworkers. She has worked out everyday for over ten years and has developed a wet dream ass with the nicest legs you will ever see. She is 5'2" and 115 pounds with pretty green eyes and hair that smells like fresh rain and she has a nice set of tits.

My wife is a living doll but she gets a little too friendly sometimes and teases until I know guys are getting hard and frustrated. She always leaves guys wondering (including me) about how far she would really go. There is no other way to describe her as anything but a big tease and I decided to call her bluff and see how far she would go, or if I could push her over the edge before she quit or reneged on a bet. I felt it was time to put up or shut up.

As the bets were placed in some of the early games I started slowly with my demons and told her to do things like run around the back yard naked or give me a blowjob while driving in the car. One night I had her masturbate with a dildo in the middle of the back yard until she came a two times.

My early favorite was blindfolding her and leading her through the house and across the patio stark naked to the garage. I put her in the car and tied her hands behind the seat and stared at her breasts jutting out and heaving up and down with her scared heavy breathing. When I opened the garage door and started the car she let out a scream because she realized that she was going for a drive around town completely naked. I told her a bet was a bet and she had to follow my directions so she took a deep breath and said that I was hers and she would not welsh on a bet. Now I was the one that was nervous knowing that the shoe will be on the other foot and I might not be as willing as she is. I backed out of the garage and stopped in the middle of the street to raise the convertible top. I drove the scenic route and was so proud of her because she knew people could see her and she sat up straight and tall.

I took her to a fairly quiet farm road outside of town and got her out of the car and bent her over the hood. I proceeded to lube her ass and without any fanfare and as I stepped up behind her I unzipped my pants pulling my aching rock hard cock. I placed my blood engorged cock head against her brown puckered ass and slowly pushed my cock past her sphincter without stopping all the way in until my balls came to rest against her pussy lips. She screamed with pain at first and I just stood still letting her get accustomed to the anal intrusion and enjoying the sight of her laid out naked in the wide open on the hood of our car under the stars and moon. Slowly she started to rock back into me and then her screams started to change to moans of pleasure. The moonlit night with her bent over the hood of the car and her hands tied behind her back was a site to behold. As my pace increased she started growling and I started slamming into her ass until we managed to cum together.

As we began to catch our breath I just couldn't believe how far I had allowed myself to go with her being exposed in public let alone fucking her in public. I knew then that the trust and love we had for each other just jumped light years ahead. I slowly withdrew my soft cock from her tight ass and watched my jism drip from her leaking ass down her legs as it glistened in the moonlight. I was glad no one had driven by but sad because I wanted to have someone see us fucking in public. I stood her up and kissed her telling her how much I loved her and was really impressed she let me lead her through all this. I sat her in her seat with her hands still tied behind her back and lowered the top on the car and that just sent her over the edge and she had an orgasm with out being touched. I drove towards home with the top down and after the first car passed us and got a good look at her I stopped and raised the top just because she was in sensory overload. That scene is burned into my brain and I will never forget that day.

I seemed to be a little more brazen about the bets than she was, so another talk ensued and she said she didn't want me to think she was perverted with some of the things she wanted me to do. I had to reassure her that the game was just that, a sexual game and I would do whatever she requested. Those words would come back to bite me in the ass.

In the beginning we played quite frequently and it seemed a little much. We decided with the new parameters we should keep the games to a Friday night once a month hoping this would keep the interest level up and not burn us out on our new found thrills.

I lost the bet in our very next game and while grinning from ear to ear she began telling me that she was going to kick it up a notch tonight and the chips could fall where they want.

She took me by the hand to the bedroom and had me stand at the end of the bed. She laid out the clothes I was to wear. Pretty easy I thought until I realized there were no shorts or socks. Yep, you guessed it, just a skirt shirt and shower shoes. The skirt she had purchased earlier looked a little like a kilt but it had a zipper on the left front leg and the shirt was more like a white see through silk wrap with arm holes. She led me to the garage and had me get in the passengers seat and off we went.

She took me to a seedy adult book store and headed straight to the counter guy. She knew that she needed to buy tokens and with a knowing nod that she gave the counter guy she led me through the store and she made me browse slowly paying special attention to the magazine rack with gay magazines. I was pretty confused by now and all the sexual visuals even the gay ones were getting me hard and the skirt was looking like a pup tent. Then we headed towards the dildo area paying special attention to the strap-on dildos.

Because I was dressed in a skirt and nervous as a cat on a hot tin roof I was too stupid to realize what was going to happen and just exactly how many notches she was going to kick it up. She just appeared to be browsing and that was making me as uncomfortable but she kept picking up the different dildos and handing them to me and asking how I liked this one, or if I liked the color, or if the size and shape of this one was too much and so it went like this for what seemed like forever. The whole time she kept rubbing them up against my face and putting them to my lips and I was really getting stressed out by all the guys looking and snickering at me as she asked these questions about plastic cocks and I was getting red as a beet. She finally decided on one and made me take it to the counter and purchase it and telling me loud enough for everyone to hear that I had made a great selection and how much fun this one will be.

She then led me to the back of the store in video area and we went into a video booth locking the door. She dropped some tokens in the machine just like she knew what she was doing and I thought this was going to be fun as she made me stand up and remove my skirt. She sat me back down and kneeling in front of me she started to rub my cock and I rolled my head back against the wall and moaned as I was getting really hard. I began to realize we were watching a bi-sexual movie with guys getting their dicks sucked by other guys and with me getting my cock rubbed and sucked in a booth naked except for my shoes my cock was as hard as it has ever been before. She looked me in the eye and told me that this was her bet and I had to due what she wanted or the game would be over for ever. Like a dummy thinking with my little head I just nodded and said "yep".

With this confirmation she raised her hand to the wall and for the first time I noticed the glory hole in it and she stuck her finger through it and waved it around for a second and pulled it back out. Well I knew it was a glory hole and what it was used for but I didn't know any of the etiquette and was startled when a cock started poking its head through the hole right next to my ear. She reminded me that a bet was a bet and I had to kiss and fondle the cock staring me in the face until she said to stop.

Ok now the demons were rearing their ugly heads and I wasn't sure if I could cross that threshold. I was mortified and I can't begin to tell you how scared at that moment I was. Keep in mind I am a large heterosexual, chauvinistic, male and at my age married as long as I have been to the same woman I had never even tasted my own cum, let alone the thought of being close to another guy or near his cock. Now I knew one of my worst demons and fears was about to come to bear and it was time to put or shut up.

I swallowed hard and reached out to grab this average sized cock and as I touched it my mind raced with a million thoughts about the size, the shape, the color, texture, and most importantly the hardness. Then I thought this guy was crazy for sticking his cock through the wall because he had no idea what was on the other side and what might happen to it. Well he was safe and I was going to prove it. I could feel how hot my face was and how excited I was getting as I began to slowly rub this strange cock. My wife started telling me what she wanted me to do to this cock and I began to follow her directions hoping she would let me get off soon as my balls were starting to ache.

I have to tell you that I was amazed how natural it became for me to fondle and rub this cock and watching it leaking its pre cum was making me want to lick it off just like an ice cream cone. So I did! As my tongue touched the head at the piss hole I became obsessed with getting it in my mouth and as I licked the shaft up and down I wanted to get in my mouth and as far down my throat as I could. As I was licking this foreign cock I could not believe how good this cock felt and how the warm soft texture with soft hair surrounding it was just making me go farther down the shaft until the head hit my gag reflex. I would pull off it and swirl my tongue around the soft bulging head and then I would lick up and down the shaft feeling the veins bulge and throb as I would fondle it. I was beginning to moan and I could feel myself getting lost and absorbed with this cock as I kept trying to deep throat it.

The sequence of events that happened next are so comical and amazing that it is hard to believe. My wife stood up and while leaning against the wall she began to feverishly rub her sopping wet pussy. As she started to have an orgasm and fell against me, this accidentally forced his cock all the way down my throat causing a flurry of comical activity. She was wedged against the wall and me in an awkward position and couldn't move and I started to gag while trying to get off this cock impaled in my throat and she was pushing against me harder and she went out of control with one of her biggest orgasms and this was just as the cock in my mouth started to twitch.

I knew what was coming and try as I might I just couldn't stop it. He started to cum in buckets right down my throat and as I began to choke I felt like I was going to die right here in a queer video booth with a cock in my mouth. I finally pushed off the cock as it shot its third round right into my eyes with the fourth round hitting me in the nose and chin. Well my wife began screaming with laughter at the site of this and fell to her knees in tears at the magnitude of the orgasm she had and the sight of her man with cum all over his face and dribbling from the corner of his mouth.

My mind raced with what just happened and my fear of tasting cum was now over. She began to recover and started kissing me and licking the freshly deposited sperm from this strange cock off my face and rubbing my cock at the same time. I can't begin to explain the feelings and emotions I had right then but I knew I really enjoyed my first time with a cock and I hoped it would happen again only more intimate.

As we recovered we weren't saying a word but our eyes were speaking volumes. I leaned my head back onto the wall wanting to reflect on what just happened. As we sat there my wife sucked on my cock and I knew it wouldn't take long before I shot my load deep in her mouth I glanced at the glory hole and a big black cock started to poke through and I just looked at my wife hoping she wouldn't make this part of the bet. I could feel myself start to go over the edge when she took my cock out of her mouth and she reached over and started to rub the big black cock jutting through the hole and it started getting harder and even much larger. She was mesmerized with this big chocolate colored cock and I was really getting nervous. She looked at me and I almost died but she knew I had that ready to get out of here or else look. She started to tease me by saying that the night was hers and I had to obey or the game was off forever the whole time she was rubbing and jacking off the black cock in her hand.

Now I was in sensory overload and hadn't cum yet and after being so close so many times I would have done just about anything in order to cum. I took a big breath and I was ready to tell her ok when she stood up and told me to stand up and get cleaned up. She then had me lean against the wall and she told me to watch her now here is the demons coming out again and I thought she was going to give this black cock a blowjob and again I was getting really nervous. She took the cock poking through the hole and began jacking it off until it began pulsing shots of cum and she guided it towards her tits and chest. I couldn't believe the effect this visual had on me and watching her with cum running down her neck and breasts as she milked the softening cock and then put her fingers to her mouth and licked the residual cum off her fingers very slowly looking me right in the eye the whole time.

With a sigh of relief I finished cleaning up with my cock sticking straight out and my balls aching like never before. She stood up and put her top on without cleaning up any of the cum dripping off her chest and then she put my kilt on. Looking like a tent she led me by one hand with the dildo in my other hand through the isles to the door. Guys were laughing and I was embarrassed like never before but I didn't care at that point because my cock and balls needed attention and they were getting really sore.

A ton of bricks were off my shoulders and as I started to breathe a sigh of relief she stopped and ordered me to undress in the parking lot. Well it was a tiny feather that knocked me over at the time and I was at a loss for words. She just looked at me and I knew exactly what that look said so without any argument I took my kilt and shirt off and stood there waiting for the next humiliation. She led me to the car and sat me down in the passenger's seat and tied my hands behind the seat. She put the top down and away we went with my cock standing straight up and my balls aching with every bump in the road.

After driving for a while I was pretty sure we were headed towards the country road that I used to take my wife's ass and I knew that we had this brand new strap on dildo that I had just picked out and I pretty much deduced that I was going to lose my anal cherry.

When we got the spot in the road famous for her anal love she stopped and got me out of the car and led me to the front. She added another dimension to the game by having me spread my legs as wide as they would go and tied my knees to the front bumper. She then bent me over the hood and tied my arms out straight to the door handles. Now here I was strapped to the hood and my cock was pressed downward between my legs and this forced my balls into the sides of my legs and I was beginning to feel some real pain now. She turned on the radio and got out to stand beside me and while dancing to the music she began to take her clothes off and throw them on the seat. Standing in the moon light and naked she was so beautiful that I was beginning to feel like I could have cum right then without even being touched. She began to strap on her weapon of choice or should I say her weapon of my choice and I have to tell you that in the light of the store the dildo looked much smaller than it did right now and I began to get scared that it would split me wide open.

She told me that if it is dry it hurts a lot worse when it goes in my ass and that I should feel how much it hurts going in if it isn't really lubed up. I panicked as she got behind me and lined up her 'cock' against my tight virgin hole and started to push it in. I was about ready to scream at the top of my lungs when she stopped and I felt some cold liquid being poured on my ass and it flowed down to my hole. I knew then that she loved me because she was lubing up my ass before she fucked it. God I love this girl I thought to myself even though I knew she was about to shove an 8" vibrating dildo into my virgin ass and fuck me until I came.

All of a sudden she stopped and kneeled down and took my cock from between my legs and with her nose in my balls and ass she started to give me a blow job. I was so turned on at that point that I came in an instant and shot huge gobs of goo into her waiting mouth. I was getting soft when she stood up and leaned over the hood and kissed me full on the lips pushing my cum into my mouth. This was the first time I tasted my own cum and I have to tell it wasn't so bad.

Now you talk about confusion here I was strapped down over the hood of our car with oil running down my ass and legs, having just gotten a premier cock sucking and for my first time a mouth full of my own cum. She told me that I should savor the flavor and to keep the noise down she produced a ball gag and placed it in my mouth and strapped it down. As I tried to digest all of these feelings and get my bearings she stepped up behind me and lined up her 'cock' to my virgin asshole without any hesitation she began to bury this anal intruder to the hilt.

This all happened so fast that before my brain had time to realize the "cock" had just passed my sphincter she stood real still. When my eyes no longer saw red and white stars I screamed into the ball gag and the muffled sound made me realize it was to no avail and that this assault on my ass was going to continue weather I liked it or not. As I inhaled a huge breath she took this as the sign to continue she grabbed my hips and began pushing this monster in my ass again until she couldn't go in any further and then she stopped to let me get accustomed to the size of the monster in my ass. When I let out a breath and inhaled again she took this as the sign I was ready to fuck and she began to pump in and out of my virgin ass at a speed that could only be compared to the Indy 500. I screamed into the gag hoped it would end soon and then I got dizzy from the pain and began to pass out. The next thing I knew she was moaning and starting to have another orgasm and the pain was gone replaced with and intense pleasure I had never known and I started to shoot another load on the hood of the car without even being touched.